JP2008516922A5 - - Google Patents
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- Publication number
- JP2008516922A5 JP2008516922A5 JP2007536122A JP2007536122A JP2008516922A5 JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5 JP 2007536122 A JP2007536122 A JP 2007536122A JP 2007536122 A JP2007536122 A JP 2007536122A JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- pyrrolidinyl
- phenyl
- methylethyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NNPOKMDCSQIRDT-HXUWFJFHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-HXUWFJFHSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-GOSISDBHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-GOSISDBHSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-LJQANCHMSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-LJQANCHMSA-N 0.000 claims 1
- YAORFRUOVGBQJQ-OAHLLOKOSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-OAHLLOKOSA-N 0.000 claims 1
- NNPOKMDCSQIRDT-FQEVSTJZSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-FQEVSTJZSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-SFHVURJKSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-SFHVURJKSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-IBGZPJMESA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-IBGZPJMESA-N 0.000 claims 1
- YAORFRUOVGBQJQ-HNNXBMFYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-HNNXBMFYSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-GOSISDBHSA-N (4-cyclobutylpiperazin-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-GOSISDBHSA-N 0.000 claims 1
- WDARRXDQPULKMV-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C(=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)F)=N1 WDARRXDQPULKMV-INIZCTEOSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-SFHVURJKSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-SFHVURJKSA-N 0.000 claims 1
- OLXZIKGIGJIHLH-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 OLXZIKGIGJIHLH-INIZCTEOSA-N 0.000 claims 1
- JTACQVQJYZNHKP-AWEZNQCLSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC2)C2CCC2)CC1 JTACQVQJYZNHKP-AWEZNQCLSA-N 0.000 claims 1
- PKXKZAADEFDOIS-KRWDZBQOSA-N (4-ethylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PKXKZAADEFDOIS-KRWDZBQOSA-N 0.000 claims 1
- GWARTCUETWOJMY-HNNXBMFYSA-N (4-pentan-3-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 GWARTCUETWOJMY-HNNXBMFYSA-N 0.000 claims 1
- RMJUTJDMAVAABO-HNNXBMFYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 RMJUTJDMAVAABO-HNNXBMFYSA-N 0.000 claims 1
- HRZIINBMVJNVJE-IBGZPJMESA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-(4-pyrrol-1-ylphenyl)pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=CC=C2)CC1 HRZIINBMVJNVJE-IBGZPJMESA-N 0.000 claims 1
- VJZWGYSVNQTUQK-ZDUSSCGKSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[2-(trifluoromethyl)pyrimidin-5-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=NC=2)C(F)(F)F)CC1 VJZWGYSVNQTUQK-ZDUSSCGKSA-N 0.000 claims 1
- YOJAJLNNCCLRHB-AWEZNQCLSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 YOJAJLNNCCLRHB-AWEZNQCLSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- VYPBIEFMFRZIFJ-LJQANCHMSA-N 1-[4-[(3r)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-LJQANCHMSA-N 0.000 claims 1
- VYPBIEFMFRZIFJ-IBGZPJMESA-N 1-[4-[(3s)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-IBGZPJMESA-N 0.000 claims 1
- URKJTOVLGKEWAE-IBGZPJMESA-N 1-[4-[(3s)-3-(4-pentan-3-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 URKJTOVLGKEWAE-IBGZPJMESA-N 0.000 claims 1
- UPMCRBZHCZHCPO-IBGZPJMESA-N 1-[4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 UPMCRBZHCZHCPO-IBGZPJMESA-N 0.000 claims 1
- AFTLCCALAJJJBT-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 AFTLCCALAJJJBT-SFHVURJKSA-N 0.000 claims 1
- PUKCWLYBBDPLFO-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]pyrrolidin-2-one Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(CCC2)=O)CC1 PUKCWLYBBDPLFO-SFHVURJKSA-N 0.000 claims 1
- QVWXADQLHGQINK-LPHOPBHVSA-N 1-[4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 QVWXADQLHGQINK-LPHOPBHVSA-N 0.000 claims 1
- NRDUEPBCTYCHEB-FQEVSTJZSA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)-1,4-diazepane-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CCC2)CC1 NRDUEPBCTYCHEB-FQEVSTJZSA-N 0.000 claims 1
- KJDLVOPRILNRCJ-IBGZPJMESA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)piperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 KJDLVOPRILNRCJ-IBGZPJMESA-N 0.000 claims 1
- DXWBJTZKDPMYNH-KRWDZBQOSA-N 3-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C#N)CC1 DXWBJTZKDPMYNH-KRWDZBQOSA-N 0.000 claims 1
- ADUVQOLQHWNHBQ-SFHVURJKSA-N 4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 ADUVQOLQHWNHBQ-SFHVURJKSA-N 0.000 claims 1
- UCHKYAUOAIHHNW-KRWDZBQOSA-N 4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 UCHKYAUOAIHHNW-KRWDZBQOSA-N 0.000 claims 1
- IVFJQUPDJYGNPR-WMZOPIPTSA-N 4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]benzonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 IVFJQUPDJYGNPR-WMZOPIPTSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QBJWLJXVGOFHFX-GOSISDBHSA-N [(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-GOSISDBHSA-N 0.000 claims 1
- QIPODOWWZRVEKL-SFHVURJKSA-N [(3s)-1-(4-imidazol-1-ylphenyl)pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=NC=C2)CC1 QIPODOWWZRVEKL-SFHVURJKSA-N 0.000 claims 1
- ZYBCHPBYMVPNQH-KRWDZBQOSA-N [(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C(=CC(=CC=2)C=2ON=C(C)N=2)F)CC1 ZYBCHPBYMVPNQH-KRWDZBQOSA-N 0.000 claims 1
- JLXVJQQSMXXOCY-SFHVURJKSA-N [(3s)-1-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C=2ON=C(C)N=2)CC1 JLXVJQQSMXXOCY-SFHVURJKSA-N 0.000 claims 1
- UYBOKBHVPBWUFH-KRWDZBQOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 UYBOKBHVPBWUFH-KRWDZBQOSA-N 0.000 claims 1
- CBCAEUGHISGMJQ-INIZCTEOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 CBCAEUGHISGMJQ-INIZCTEOSA-N 0.000 claims 1
- VBSGTTPSUKPZJQ-SFHVURJKSA-N [(3s)-1-[4-(1,2-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=CC=2)CC1 VBSGTTPSUKPZJQ-SFHVURJKSA-N 0.000 claims 1
- BKPMNQNQXRJZKV-SFHVURJKSA-N [(3s)-1-[4-(1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC=NC=2)CC1 BKPMNQNQXRJZKV-SFHVURJKSA-N 0.000 claims 1
- VGBIKTCJQQKEFX-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-4-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)OC=2)CC1 VGBIKTCJQQKEFX-IBGZPJMESA-N 0.000 claims 1
- UBRPQLXMDZVHCP-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NC=2)CC1 UBRPQLXMDZVHCP-IBGZPJMESA-N 0.000 claims 1
- PCEWCRUEPDUGSU-IBGZPJMESA-N [(3s)-1-[4-(2-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(=NC=C2)C)CC1 PCEWCRUEPDUGSU-IBGZPJMESA-N 0.000 claims 1
- YYNFVEZVQLHDGC-IBGZPJMESA-N [(3s)-1-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CCC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C(C)C)=N1 YYNFVEZVQLHDGC-IBGZPJMESA-N 0.000 claims 1
- PATUCRXRMASYJU-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PATUCRXRMASYJU-IBGZPJMESA-N 0.000 claims 1
- WHCWUQZKDPMIGH-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 WHCWUQZKDPMIGH-IBGZPJMESA-N 0.000 claims 1
- QBJWLJXVGOFHFX-SFHVURJKSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-SFHVURJKSA-N 0.000 claims 1
- CQFSDSNLSQURSR-LPHOPBHVSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-[(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 CQFSDSNLSQURSR-LPHOPBHVSA-N 0.000 claims 1
- PXVPPTFSYIKJBE-IBGZPJMESA-N [(3s)-1-[4-(4-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=C(C)N=C2)CC1 PXVPPTFSYIKJBE-IBGZPJMESA-N 0.000 claims 1
- NIXPOQHPJVUNEI-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)ON=2)CC1 NIXPOQHPJVUNEI-SFHVURJKSA-N 0.000 claims 1
- AWSWXQJSGZQQOU-IBGZPJMESA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 AWSWXQJSGZQQOU-IBGZPJMESA-N 0.000 claims 1
- RHMDXLFQFOBXOH-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 RHMDXLFQFOBXOH-SFHVURJKSA-N 0.000 claims 1
- IGSLFRDFOPKRTK-QFIPXVFZSA-N [(3s)-1-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)CC1 IGSLFRDFOPKRTK-QFIPXVFZSA-N 0.000 claims 1
- OJDIWUZFITXDRO-INIZCTEOSA-N [(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C=2ON=C(C)N=2)CC1 OJDIWUZFITXDRO-INIZCTEOSA-N 0.000 claims 1
- MSKUPINGSAZGTP-GJZGRUSLSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 MSKUPINGSAZGTP-GJZGRUSLSA-N 0.000 claims 1
- QPDUYTMJXPZQDA-FQEVSTJZSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 QPDUYTMJXPZQDA-FQEVSTJZSA-N 0.000 claims 1
- HTSWAPRVWBKBGO-SFHVURJKSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 HTSWAPRVWBKBGO-SFHVURJKSA-N 0.000 claims 1
- LXKMZMNNAKJQFD-IBGZPJMESA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 LXKMZMNNAKJQFD-IBGZPJMESA-N 0.000 claims 1
- QEZZAHLGBVDWNB-KRWDZBQOSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 QEZZAHLGBVDWNB-KRWDZBQOSA-N 0.000 claims 1
- GKAQOFAZTNGKLA-HNNXBMFYSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 GKAQOFAZTNGKLA-HNNXBMFYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005533 aryl carboxamido group Chemical group 0.000 claims 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0423005A GB0423005D0 (en) | 2004-10-15 | 2004-10-15 | Novel compounds |
| GB0508441A GB0508441D0 (en) | 2004-10-15 | 2005-04-26 | Novel compounds |
| PCT/EP2005/011371 WO2006040192A1 (en) | 2004-10-15 | 2005-10-13 | Pyrrolidine derivatives as histamine receptors ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008516922A JP2008516922A (ja) | 2008-05-22 |
| JP2008516922A5 true JP2008516922A5 (enExample) | 2008-11-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2007536122A Withdrawn JP2008516922A (ja) | 2004-10-15 | 2005-10-13 | ヒスタミン受容体リガンドとしてのピロリジン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20080045506A1 (enExample) |
| EP (1) | EP1802307B1 (enExample) |
| JP (1) | JP2008516922A (enExample) |
| AR (1) | AR051391A1 (enExample) |
| AT (1) | ATE387202T1 (enExample) |
| DE (1) | DE602005005080T2 (enExample) |
| DK (1) | DK1802307T3 (enExample) |
| ES (1) | ES2303280T3 (enExample) |
| HR (1) | HRP20080227T3 (enExample) |
| PL (1) | PL1802307T3 (enExample) |
| PT (1) | PT1802307E (enExample) |
| SI (1) | SI1802307T1 (enExample) |
| WO (1) | WO2006040192A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| CN101472887A (zh) | 2006-06-23 | 2009-07-01 | 艾博特公司 | 作为组胺h3受体调节物的环丙胺衍生物 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| BRPI0815591B8 (pt) | 2007-08-22 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, e, uso de um composto. |
| WO2009030716A1 (en) | 2007-09-06 | 2009-03-12 | Glaxo Group Limited | Piperazine derivative having affinity for the histamine h3 receptor |
| ES2428716T3 (es) | 2008-02-22 | 2013-11-11 | F. Hoffmann-La Roche Ag | Moduladores de beta-amiloide |
| CA2721303C (en) | 2008-05-08 | 2016-06-28 | Evotec Ag | Azetidines and cyclobutanes as histamine h3 receptor antagonists |
| US8236792B2 (en) | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| JP5530438B2 (ja) * | 2008-08-06 | 2014-06-25 | ファイザー・リミテッド | Ｍｃ４作動薬としてのジアゼピンおよびジアゾカン化合物 |
| JP5502089B2 (ja) | 2008-10-09 | 2014-05-28 | エフ．ホフマン−ラ ロシュ アーゲー | アミロイドβのモジュレーター |
| WO2010052199A1 (en) | 2008-11-10 | 2010-05-14 | F. Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
| US8912176B2 (en) | 2009-02-02 | 2014-12-16 | Evotec Ag | Azetidines as histamine H3 receptor antagonists |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2011016559A1 (ja) * | 2009-08-07 | 2011-02-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| AU2011218492B2 (en) | 2010-02-18 | 2014-11-13 | Astrazeneca Ab | New crystalline form of a cyclopropyl benzamide derivative |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| AU2023247609A1 (en) * | 2022-03-31 | 2024-10-17 | Bebetter Med Inc. | 1,4-diheterocyclic substituted aromatic ring or aromatic heterocyclic compound and use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL128428A0 (en) * | 1996-08-14 | 2000-01-31 | Zeneca Ltd | Substituted pyrimidine derivatives and their pharmaceutical use |
| DE10034338C2 (de) * | 2000-07-14 | 2002-06-20 | Forschungszentrum Juelich Gmbh | Mehrpoliges kaskadierendes Quardrupel-Bandpaßfilter auf der Basis dielektrischer Dual-Mode-Resonatoren |
| JPWO2003062234A1 (ja) * | 2002-01-23 | 2005-05-19 | 山之内製薬株式会社 | キノキサリン化合物 |
| JP2006505590A (ja) * | 2002-10-23 | 2006-02-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ヒスタミンｈ３受容体調節物質としてのフェニルピペリジンおよびフェニルピロリジン |
| AU2004238447C1 (en) * | 2003-04-23 | 2009-06-11 | Glaxo Group Limited | Piperazine derivatives and their use for the treatment of neurological and psychiatric diseases |
-
2005
- 2005-10-13 PL PL05802453T patent/PL1802307T3/pl unknown
- 2005-10-13 JP JP2007536122A patent/JP2008516922A/ja not_active Withdrawn
- 2005-10-13 US US11/576,968 patent/US20080045506A1/en not_active Abandoned
- 2005-10-13 DE DE602005005080T patent/DE602005005080T2/de not_active Expired - Lifetime
- 2005-10-13 HR HR20080227T patent/HRP20080227T3/xx unknown
- 2005-10-13 EP EP05802453A patent/EP1802307B1/en not_active Expired - Lifetime
- 2005-10-13 WO PCT/EP2005/011371 patent/WO2006040192A1/en not_active Ceased
- 2005-10-13 PT PT05802453T patent/PT1802307E/pt unknown
- 2005-10-13 ES ES05802453T patent/ES2303280T3/es not_active Expired - Lifetime
- 2005-10-13 DK DK05802453T patent/DK1802307T3/da active
- 2005-10-13 SI SI200530241T patent/SI1802307T1/sl unknown
- 2005-10-13 AT AT05802453T patent/ATE387202T1/de not_active IP Right Cessation
- 2005-10-13 AR ARP050104299A patent/AR051391A1/es unknown
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